Synthesis and properties of novel poly(arylene ether)s and poly(arylene thioether)s based on a pyridazine biphenol or a phthalazine biphenol

Novel sulfur-containing biphenol monomers were prepared in high yields by the reaction of 4-mercaptophenol with chloropyridazine or chlorophthalazine compounds. High-molecular-weight poly(arylene ether)s were synthesized by a nucleophilic substitution reaction between these sulfur-containing monomers and activated difluoro aromatic compounds. The inherent viscosities of these polymers ranged from 0.34 to 0.93 dL/g. The poly(pyridazine)s exhibited glass-transition temperatures greater than 165 degrees C. The poly(phthalazine)s showed higher glass-transition temperatures than the poly(pyridazine)s. A polymer synthesized from a bisphthalazinebiphenol and bis(4-fluorophenyl)sulfone had the highest glass-transition temperature (240 degrees C). The thermal stabilities of the poly(pyridazine)s and poly(phthalazine)s showed similar patterns of decomposition, with no significant weight loss below 390 degrees C. The poly(phthalazine)s were soluble in chlorinated solvents such as chloroform, and the poly(pyridazine)s were soluble in dipolar aprotic solvents such as N,N'-dimethylacetamide. The soluble poly (pyridazine)s and poly(phthalazine)s could be cast into flexible films from solution. (c) 2006 Wiley Periodicals, Inc.